4-Iodophenol → HCID 19261706, compound

HRID 1519720Notes

Reaction equation

HRID 1519720 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1.[I:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.[O:28]1[CH2:33][CH2:32][N:31]([CH2:34][CH2:35]O)[CH2:30][CH2:29]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[I:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:35][CH2:34][N:31]2[CH2:32][CH2:33][O:28][CH2:29][CH2:30]2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 108944-IodophenolHCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 87147022ethyl (NE)-N-ethoxycarbonyliminocarbamate;toluene

Product 1

HCID 19261706HCID 19261706, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

40% DEAD/toluene (2.5 mL) was added to a THF (30 mL) solution of 4-iodophenol (1.0 g), 2-morpholinoethanol (0.72 g) and triphenylphosphine (1.4 g) under ice cooling, and the mixture was stirred for 17 hours at room temperature. After the solvents were distilled off, the resulting residue was purified by NH type silica gel chromatography (gradient elution with hexane/ethyl acetate=90/0→60/40) to obtain 4-[2-(4-iodophenoxy)ethyl]morpholine (colorless oil) (1.4 g, 93%).

Workup

  1. distillationAfter the solvents were distilled off
  2. customthe resulting residue was purified by NH type silica gel chromatography (gradient elution with hexane/ethyl acetate=90/0→60/40)

Sources & evidence

ORD record
ord-0b6d174f2c7c425089c46a00d9c1aae3
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

Loading…